EP1963301A1 - Verfahren zur herstellung von glycerincarbonat - Google Patents
Verfahren zur herstellung von glycerincarbonatInfo
- Publication number
- EP1963301A1 EP1963301A1 EP06794013A EP06794013A EP1963301A1 EP 1963301 A1 EP1963301 A1 EP 1963301A1 EP 06794013 A EP06794013 A EP 06794013A EP 06794013 A EP06794013 A EP 06794013A EP 1963301 A1 EP1963301 A1 EP 1963301A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- glycerol
- preparation
- glycerol carbonate
- carbonate
- catalyst
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D317/34—Oxygen atoms
- C07D317/36—Alkylene carbonates; Substituted alkylene carbonates
Definitions
- the invention relates to a process for the preparation of glycerol carbonate with low glycerol content.
- Glycerol carbonate is used as an intermediate for the preparation of pharmaceuticals and pesticides and for the production of (meth) acrylates as a precursor for coating resins. A high purity is therefore advantageous.
- EP 739888 describes a process for the preparation of glycerol carbonate from ethylene carbonate and glycerol with Amberlyst (ion exchanger) or zeolites, in which at least 2-4% glycerol are contained in the crude product.
- JP 2001172277 the production of glycerol carbonate is claimed by transesterification of dimethyl carbonate with glycerol under basic catalysis.
- the glycerine carbonate has a purity of 95% glycerol content of 1, 6%.
- EP 1423377 describes a purification of a glycerol carbonate by means of an anhydrous base. The work-up step lowers the glycerol content to 3.5-4.1% by weight.
- the object of the invention was to produce glycerol carbonate in high purity and with high yields.
- the object was achieved by a process for the preparation of glycerol carbonate, characterized in that glycerol with dialkyl carbonates or cyclic carbonates in the presence of a basic catalyst from a mixture of at least two components from the group of metal hydroxides and / or, chlorides and / or oxides is transesterified.
- the starting materials used are dialkyl carbonates, preferably dimethyl carbonate or diethyl carbonate.
- cyclic carbonates preferably ethylene carbonate can be used.
- the basic catalyst or the catalyst mixture is used in amounts of 0.01 to 10 wt .-%.
- basic catalysts from the group of alkali metal or alkaline earth metal hydroxides, chlorides and / or oxides mixtures of 2 or 3 components from the group of lithium hydroxides or potassium hydroxides or calcium hydroxides and / or lithium chlorides or potassium chlorides or calcium chlorides and / or calcium oxides are preferably used.
- Preferred mixing ratios for chlorides with hydroxides are 1 to 99% to 99 to 1%, more preferably 15 to 85% to 30 to 70%, preferably for LiCl: Ca (OH) 2 20 to 80%.
- Preferred mixing ratios for chlorides with oxides are 1 to 99% to 99 to 1%, particularly preferably 15 to 85% to 30 to 70%, preferably for LiCl: CaO at 20 to 80%.
- the transesterification takes place at temperatures from 60 to 150 0 C, preferably at 70-85 0 C.
- the transesterification is preferably carried out under normal pressure. However, attempts at transesterification in a vacuum have also been successful. Likewise, it is possible to work under elevated pressure.
- Fields of use for glycerol carbonate produced by the process according to the invention are, for example, a precursor for paints and adhesives.
- the batch is introduced into the reaction apparatus and heated under reflux for 9 hours. After cooling, the catalyst is separated by filtration. The low boilers are then distilled off on a rotary evaporator in vacuo, then filtered again and the crude product.
- the batch is introduced into the reaction apparatus and heated under reflux for 8 hours. After cooling, the catalyst is separated by filtration. The low boilers are then distilled off on a rotary evaporator in vacuo, then filtered again and the crude product.
- the batch is introduced into the reaction apparatus and heated under reflux for 8 hours. After cooling, the catalyst is separated by filtration. The low boilers are then distilled off on a rotary evaporator in vacuo, then filtered again and the crude product. Attempts to produce glycerin carbonate
- Examples B1, B2, B3 and B4 show high product yields and very low glycerol levels in the product.
- Example 4 additionally shows a low concentration of glycerol methyl dicarbonate.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Polyesters Or Polycarbonates (AREA)
Description
Claims
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102005060732A DE102005060732A1 (de) | 2005-12-16 | 2005-12-16 | Verfahren zur Herstellung von Glycerincarbonat |
PCT/EP2006/067279 WO2007071470A1 (de) | 2005-12-16 | 2006-10-11 | Verfahren zur herstellung von glycerincarbonat |
Publications (2)
Publication Number | Publication Date |
---|---|
EP1963301A1 true EP1963301A1 (de) | 2008-09-03 |
EP1963301B1 EP1963301B1 (de) | 2011-03-02 |
Family
ID=37685663
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP06794013A Not-in-force EP1963301B1 (de) | 2005-12-16 | 2006-10-11 | Verfahren zur herstellung von glycerincarbonat |
Country Status (15)
Country | Link |
---|---|
US (1) | US7790908B2 (de) |
EP (1) | EP1963301B1 (de) |
JP (1) | JP2009519286A (de) |
KR (1) | KR20080078835A (de) |
CN (1) | CN101287720A (de) |
AT (1) | ATE500238T1 (de) |
AU (1) | AU2006328838A1 (de) |
BR (1) | BRPI0619887A2 (de) |
CA (1) | CA2630242A1 (de) |
DE (2) | DE102005060732A1 (de) |
NZ (1) | NZ566676A (de) |
RU (1) | RU2008128560A (de) |
TW (1) | TW200732318A (de) |
WO (1) | WO2007071470A1 (de) |
ZA (1) | ZA200802049B (de) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2014033045A1 (de) | 2012-08-28 | 2014-03-06 | Bayer Materialscience Ag | Bindemittel mit cyclischen carbonatstrukturen |
WO2014033046A1 (de) | 2012-08-28 | 2014-03-06 | Bayer Materialscience Ag | Isocyanatfunktionelle cyclische carbonate |
Families Citing this family (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE10314776A1 (de) | 2003-03-31 | 2004-10-14 | Rohmax Additives Gmbh | Schmierölzusammensetzung mit guten Reibeigenschaften |
DE102006006200B4 (de) * | 2006-02-09 | 2008-01-10 | Röhm Gmbh | Wässrige N-Methylol-methacrylamid-Methacrylamid-Mischung |
CN101328124B (zh) * | 2008-08-01 | 2011-01-12 | 河北工业大学 | 一种合成二甘醇双烯丙基碳酸酯的酯交换法 |
EP2350041A1 (de) * | 2008-10-17 | 2011-08-03 | Basf Se | Verfahren und katalysatoren zur herstellung von cyclischen carbonaten |
JP2010202624A (ja) * | 2009-03-06 | 2010-09-16 | Japan Advanced Institute Of Science & Technology Hokuriku | グリセリンカーボネートの製造方法 |
ES2355782B1 (es) * | 2009-06-16 | 2012-02-03 | REPSOL YPF, S.A. (Titular al 75%) | Catalizadores heterogéneos para la obtención de carbonato de glicerol. |
FR2954313B1 (fr) * | 2009-12-21 | 2014-08-01 | Centre Nat Rech Scient | Procede de preparation de dithiocarbamates notamment a partir de polyols du type glycerol. |
CN102250051A (zh) * | 2010-05-18 | 2011-11-23 | 中国科学院兰州化学物理研究所 | 一种碳酸甘油酯的制备方法 |
WO2012095293A2 (en) | 2011-01-14 | 2012-07-19 | Cognis Ip Management Gmbh | Process for the synthesis of compounds from cyclic carbonates |
CN103467435B (zh) * | 2013-09-11 | 2016-02-24 | 北京林业大学 | 一种制备甘油碳酸酯的方法 |
CN103524476B (zh) * | 2013-10-16 | 2016-03-09 | 广西科学院 | 多元反应体系合成甘油碳酸酯联产短碳链碳酸酯的方法 |
CN107148415B (zh) * | 2014-10-23 | 2020-11-13 | 建筑研究和技术有限公司 | 制备甘油酸碳酸酯的方法 |
CN105709785B (zh) * | 2014-12-05 | 2018-10-09 | 临沂中通科技有限公司 | 一种用于制备碳酸甘油酯的催化剂、其使用方法及其应用 |
CN108484564A (zh) * | 2018-05-02 | 2018-09-04 | 西安石油大学 | 一种复合固体碱催化快速制备碳酸甘油酯的方法 |
CN110652979B (zh) * | 2018-06-28 | 2022-07-26 | 张家港市国泰华荣化工新材料有限公司 | 采用混合催化剂制备碳酸甘油酯的方法 |
CN109824881B (zh) * | 2019-01-30 | 2020-08-18 | 华南理工大学 | 一种多元环碳酸酯树脂及其常压下快速制备方法与应用 |
CN113210020A (zh) * | 2021-05-14 | 2021-08-06 | 江南大学 | 催化甘油酯交换制备碳酸甘油酯的催化剂及其制备方法 |
CN113509922B (zh) * | 2021-07-13 | 2022-09-16 | 中国科学院山西煤炭化学研究所 | 一种用于合成脂肪族碳酸酯的催化剂及其制备方法和应用 |
CN113908877A (zh) * | 2021-11-15 | 2022-01-11 | 浙江工业大学 | 一种白云石-硝酸盐/氯化物复合催化剂及其制备方法与应用 |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2915529A (en) | 1957-04-15 | 1959-12-01 | Jefferson Chem Co Inc | Method for preparing glycerin carbonate |
CA2051488A1 (en) | 1990-09-20 | 1992-03-21 | Stephen W. King | Processes for the preparation of carboxylated compounds |
DE4225870A1 (de) * | 1992-08-05 | 1994-02-10 | Basf Ag | Verfahren zur Herstellung von Glycerincarbonat |
JP3540822B2 (ja) * | 1993-05-25 | 2004-07-07 | 丸善ケミカル株式会社 | グリセロールカーボネートの製造方法 |
FR2733232B1 (fr) * | 1995-04-24 | 1997-06-13 | Organisation Nationale Interpr | Procede de fabrication de carbonate de glycerol a partir de glycerol et d'un carbonate organique cyclique, en particulier carbonate d'ethylene ou de propylene |
JP4284802B2 (ja) * | 1999-12-21 | 2009-06-24 | 宇部興産株式会社 | 4−ヒドロキシメチル−1,3−ジオキソラン−2−オンの製造法 |
MY139064A (en) | 2001-11-13 | 2009-08-28 | Shell Int Research | METHOD FOR THE CATALYTIC CONVERSION OF ALKYLENE CARBONATE WITH Mg, A1 MIXED (HYDR) OXIDE CATALYST AND ITS USE THEREFORE |
-
2005
- 2005-12-16 DE DE102005060732A patent/DE102005060732A1/de not_active Withdrawn
-
2006
- 2006-10-11 AU AU2006328838A patent/AU2006328838A1/en not_active Abandoned
- 2006-10-11 CA CA002630242A patent/CA2630242A1/en not_active Abandoned
- 2006-10-11 AT AT06794013T patent/ATE500238T1/de active
- 2006-10-11 EP EP06794013A patent/EP1963301B1/de not_active Not-in-force
- 2006-10-11 JP JP2008544904A patent/JP2009519286A/ja active Pending
- 2006-10-11 NZ NZ566676A patent/NZ566676A/en unknown
- 2006-10-11 BR BRPI0619887-2A patent/BRPI0619887A2/pt not_active IP Right Cessation
- 2006-10-11 US US12/088,093 patent/US7790908B2/en not_active Expired - Fee Related
- 2006-10-11 CN CNA2006800383318A patent/CN101287720A/zh active Pending
- 2006-10-11 RU RU2008128560/04A patent/RU2008128560A/ru not_active Application Discontinuation
- 2006-10-11 KR KR1020087014449A patent/KR20080078835A/ko not_active Application Discontinuation
- 2006-10-11 DE DE502006009032T patent/DE502006009032D1/de active Active
- 2006-10-11 WO PCT/EP2006/067279 patent/WO2007071470A1/de active Application Filing
- 2006-12-13 TW TW095146699A patent/TW200732318A/zh unknown
-
2008
- 2008-03-04 ZA ZA200802049A patent/ZA200802049B/xx unknown
Non-Patent Citations (1)
Title |
---|
See references of WO2007071470A1 * |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2014033045A1 (de) | 2012-08-28 | 2014-03-06 | Bayer Materialscience Ag | Bindemittel mit cyclischen carbonatstrukturen |
WO2014033046A1 (de) | 2012-08-28 | 2014-03-06 | Bayer Materialscience Ag | Isocyanatfunktionelle cyclische carbonate |
US9556304B2 (en) | 2012-08-28 | 2017-01-31 | Covestro Deutschland Ag | Binder with cyclic carbonate structures |
US9567313B2 (en) | 2012-08-28 | 2017-02-14 | Covestro Deutschland Ag | Isocyanate-functional cyclic carbonates |
Also Published As
Publication number | Publication date |
---|---|
RU2008128560A (ru) | 2010-01-27 |
DE502006009032D1 (de) | 2011-04-14 |
ZA200802049B (en) | 2009-09-30 |
TW200732318A (en) | 2007-09-01 |
AU2006328838A1 (en) | 2007-06-28 |
KR20080078835A (ko) | 2008-08-28 |
JP2009519286A (ja) | 2009-05-14 |
NZ566676A (en) | 2010-06-25 |
CA2630242A1 (en) | 2007-06-28 |
US7790908B2 (en) | 2010-09-07 |
BRPI0619887A2 (pt) | 2011-10-25 |
DE102005060732A1 (de) | 2007-06-21 |
WO2007071470A1 (de) | 2007-06-28 |
EP1963301B1 (de) | 2011-03-02 |
US20080255372A1 (en) | 2008-10-16 |
ATE500238T1 (de) | 2011-03-15 |
CN101287720A (zh) | 2008-10-15 |
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